All of the sites allow you to search by preferred times but none to my knowledge allow you to set up alerts for specific arrival/departure times. Interesting idea to have sites sort flights by legroom cost, hadn’t thought of that and certainly have not seen it. Southwest used to have an alert tool called Ding, but no longer. You can include Southwest on Google flights but in its search results it only shows scheduling, you’re redirected to the Southwest website for pricing. Sorry I can’t help you more with your wish list but I sure do thank you for your comments and questions.
The second upgrade tip is to check the upgrade availability frequently. Although upgrade seats may not be available at the time you purchased the coach ticket the inventory for upgrades is constantly changing, right up until the time of departure. You can check with your airline every day or several times a week or you can use an alert service from some online services such as ExpertFlyer.com. ExpertFlyer.com now offers Flight Alerts, a service that allows you to program your actual flight or series of preferred flights for an upgrade or award. Flight Alerts will automatically search for open availability and notify you immediately once it locates a seat. The notification can be sent to three (3) different addresses including personal or work email, cell phone or PDA so no matter where you are or what you're doing, you will be notified the moment Flight Alerts finds the Premium seat you're looking for. Flight Alerts, or a similar notification program, can also assist you in finding seats using only awards miles.